Synthesis of novel ADPR analogues: substitution of pyrophosphate linkage by dipeptide

Abstract

Abstract:

For investigating the biological function of ADPR, four novel analogues (compounds 2–5) in which the pyrophosphate linkage was replaced by the aspartic acid dipeptide were synthesized. 5'-Amino adenosine or its analogues was used as the starting material, liquid phase peptide synthesis strategy was used to construct these ADPR analogues. The structures were characterized by 1H NMR and HRMS spectra. This study provides a versatile synthesis of peptide modified ADPR analogues and helps to understand the structure-activity relationship of ADPR.

Key words: ADPR, ADPR, Nucleoside, Nucleoside, Analogues, Analogues, Synthesis, Synthesis

CLC Number:

R916

Supporting:

Chao Zhang, Zhen-Jun Yang, Liang-Ren Zhang^*, Li-He Zhang. Synthesis of novel ADPR analogues: substitution of pyrophosphate linkage by dipeptide[J]. .

References

[1] Howard, M.; Grimaldi, J.C.; Bazan, J.F.; Lund, F.E.; Santos-Argumedo, L.; Parkhouse, R.M.; Walseth, T.F.; Lee, H.C. Science.1993, 262: 1056–1059.
[2] Lee, H.C.; Zocchi, E.; Guida, L.; Franco, L.; Benatti, U.; De Flora, A. Biochem. Biophys. Res. Commun. 1993, 191: 639–645.
[3] Takasawa, S.; Tohgo, A.; Noguchi, N.; Koguma, T.; Nata, K.; Sugimoto, T.; Yonekura, H.; Okamoto, H. J. Biol. Chem. 1993, 268: 26052–26054.
[4] Kim, V.D.; Marie, E.M. Org. Lett. 2004, 6: 3461–3464.
[5] Perraud, A.L.; Fleig, A.; Dunn, C.A.; Bagley, L.A.; Launay, P.; Schmitz, C.; Stokes, A.J.; Zhu, Q.; Bessman, M.J.; Penner, R.; Kinet, J.P.; Scharenberg, A.M. Nature. 2001, 411: 595–599.
[6] Perraud, A.L.; Schmitz, C.; Scharenberg, A.M. Cell Calcium. 2003, 33: 519–531.
[7] Perraud, A.L.; Knowles, H.M.; Schmitz, C. Mol. Immunol. 2004, 41: 657–673.
[8] Gasser, A.; Glassmeier, G.; Fliegert, R.; Langhorst, M.F.; Meinke, S.; Hein, D.; Krüger, S.; Weber, K.; Heiner, I.; Oppenheimer, N.; Schwarz, J.R.; Guse, A.H. J. Biol. Chem. 2006, 281: 2489–2496.
[9] Aarts, M.M.; Tymianski, M. Pflugers Arch-Eur. J. Physiol. 2005, 451: 243–249.
[10] Guse, A.H.; Gu, X.; Zhang, L.; Weber, K.; Kramer, E.; Yang, Z.; Jin, H.W.; Li, Q.; Carrier, L.; Zhang, L. J. Biol. Chem. 2005, 280: 15952–15959.
[11] Ti, G.S.; Gaffney, B.L.; Jones, R.A. J. Am. Chem. Soc. 1982, 104: 1316–1319.
[12] Shuto, S.; Obara, T.; Toriya, M.; Hosoya, M.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1992, 35, 324–331.
[13] Ciuffreda, P.; Loseto, A.; Santaniello, E. Tetrahedron. 2002, 58: 5767–5771.
[14] Liu, F.; Austin, D.J. Tetrahedron Lett. 2001, 42: 3153–3154.
[15] Paquette, L.A.; Bailey, S. J. Org. Chem. 1995, 60: 7849–7856.
[16] Bosch, M.P.; Campos, F.; Niubo, I.; Rosell, G.; Diaz, J. L.; Brea, J.; Loza, M. I.; Guerrero, A. J. Med. Chem. 2004, 47: 4041–4053.
[17] Gholam, H.H.; Morteza, Z.; Ali, A.J.; Hashem, S. Helv. Chim. Acta. 1987, 70: 219–231.
[18] Maguire, A.R.; Meng, W.D.; Roberts, S.M.; Willetts, A.J. J. Chem. Soc. Perkin Trans. 1993, 15, 1795–1808.
[19] Wicks, Z.W.; Chen, G.F. J. Org. Chem. 1979, 44: 1244–1247.